Founders Guilt & More.

Saajan Jain
4 min readOct 9, 2022

“I’m living everyday like a hustle. Another drug to juggle. Another day, another struggle.” — Notorious BIG

Recently I met a friend who is a founder & he told me that he has not taken a break in the last two years or so. As he is constantly hustling & building the business, it makes him feel guilty even to think about taking a break. Though it's a big concern, I do relate to him. I myself have been at it working for the last four years now & work has been constantly on top of my mind even if I go on a short vacation.

I call this phenomenon ‘Founders Guilt’. Read about it. The best way to describe this feeling is when you want your every second on weekdays or weekends to be productive. I have a feeling that the business won’t move if I don’t check my emails, check in with my team, or check in with my clients. Even getting sick where your body needs rest makes you feel guilty as you want to do some things but you can’t. Again, this has nothing to do with motivation. If I was motivated enough, I would know when to slow down & when to run. It has to do a lot with personality which has been developed over time

When a person becomes an entrepreneur & sees the market either they want to emulate a known entrepreneur & his work ethic [Hint: Elon Musk] or set a moving goal post so that they keep climbing up at a rapid pace as the thought is that If I don’t go fast & be productive every minute, the business will die. This leads to burnout which can be either a mental breakdown or a physical breakdown & trust me you can’t afford either. It's better to have some losses in your books than your health.

My journey has now been six years working for myself or you can call it two years of freelancing & four years of running a business. I have had my share of founders' guilt & burnout every now & then & I am still learning to show up everyday for work. Sometimes with excitement, sometimes with agony. One thing which is becoming clearer to me running a business is that there will never be a destination where I will reach & feel like I have won the world, the feeling has to start building in the journey itself. Hence, I focus a lot on small wins — On the work & off the work

Completing a book — If you read books, try completing a book once. I feel like a small win that day. It's a lengthy book? Read short stories.
Doing a physical activity — I used to run in the past but I just don’t enjoy it anymore. Thinking of running itself makes me tired of not stepping out at all. Hence, I started daily walks. Can’t do it daily? Maybe try 2–3 times a week & walk as per your capacity. 30mins? 60mins? 15mins? Doesn’t matter. Idea is to have some movement. I have also started swimming just for fun with no compulsion to do it daily.
Talking to founders — Just talking & not having any takeaways most of the time. This will make you understand that other people who are on the same path also have similar problems & you will go easy on yourself one day at a time.
Responding — When faced with a strong reaction to a situation, I tend to step back, have a breather & put up an honest response so that I can sleep well. Taking a breather & responding to a person or a situation makes a small win as that averts a crisis in making.
Seeking ‘real’ help- I have contemplated a lot on whether I should seek therapy or not coz nothing major felt wrong in my life. Money, relationships, and health are all good (not the best) but not suffering either. Still, living with continuous anxiety is like walking around with a boulder on your head which you should not be lifting at all. Hence, I would be going to therapy & have started taking steps toward finding one. I think I might need it.

Yes, hustle is important but you need to enjoy the journey & slow down if needed.

Nature does not hurry, yet everything is accomplished.― Lao Tzu